RU2287530C2 - Лактамные соединения и их фармацевтическое использование - Google Patents

Лактамные соединения и их фармацевтическое использование Download PDF

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Publication number: RU2287530C2
Authority: RU; Russia
Prior art keywords: group; substituent; alkyl; phenyl; ring
Prior art date: 2000-12-01

Application number

RU2003116126/04A

Other languages

English (en)

Russian (ru)

Other versions

RU2003116126A (ru

Inventor

Юкио ЙИНО (JP)

Юкио ЙИНО

Такао ИКЕНОУЕ (JP)

Такао ИКЕНОУЕ

Нобуо КОНДО (JP)

Нобуо КОНДО

Хироюки МАЦУЕДА (JP)

Хироюки МАЦУЕДА

Тосихиро ХАТАНАКА (JP)

Тосихиро ХАТАНАКА

Риусуке ХИРАМА (JP)

Риусуке ХИРАМА

Йоко МАСУЗАВА (JP)

Йоко МАСУЗАВА

Фумио ОХТА (JP)

Фумио ОХТА

Акийо ЯМАЗАКИ (JP)

Акийо ЯМАЗАКИ

Original Assignee

Адзиномото Ко., Инк.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-12-01

Filing date

2001-11-29

Publication date

2006-11-20

2001-11-29 Application filed by Адзиномото Ко., Инк. filed Critical Адзиномото Ко., Инк.

2004-11-27 Publication of RU2003116126A publication Critical patent/RU2003116126A/ru

2006-11-20 Application granted granted Critical

2006-11-20 Publication of RU2287530C2 publication Critical patent/RU2287530C2/ru

Links

-1 Lactam compounds Chemical class 0.000 title claims abstract description 260
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 67
235000000346 sugar Nutrition 0.000 claims abstract description 41
125000002252 acyl group Chemical group 0.000 claims abstract description 37
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
125000000217 alkyl group Chemical group 0.000 claims abstract description 31
150000003839 salts Chemical class 0.000 claims abstract description 28
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 19
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
238000011282 treatment Methods 0.000 claims abstract description 15
125000004423 acyloxy group Chemical group 0.000 claims abstract description 14
229910052799 carbon Inorganic materials 0.000 claims abstract description 13
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 13
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 12
125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 10
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 9
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims abstract description 8
208000007342 Diabetic Nephropathies Diseases 0.000 claims abstract description 8
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 8
208000033679 diabetic kidney disease Diseases 0.000 claims abstract description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 8
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims abstract description 6
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims abstract description 6
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical group C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims abstract description 6
125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 6
125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
125000001544 thienyl group Chemical group 0.000 claims abstract description 6
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
125000004434 sulfur atom Chemical group 0.000 claims abstract description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 15
125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims abstract 6
125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims abstract 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 3
125000001424 substituent group Chemical group 0.000 claims description 98
125000003277 amino group Chemical group 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 12
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
239000004480 active ingredient Substances 0.000 claims description 10
125000001931 aliphatic group Chemical group 0.000 claims description 10
125000002950 monocyclic group Chemical group 0.000 claims description 8
208000032131 Diabetic Neuropathies Diseases 0.000 claims description 7
206010063547 Diabetic macroangiopathy Diseases 0.000 claims description 7
206010012689 Diabetic retinopathy Diseases 0.000 claims description 7
208000002705 Glucose Intolerance Diseases 0.000 claims description 7
208000008589 Obesity Diseases 0.000 claims description 7
235000020824 obesity Nutrition 0.000 claims description 7
201000009104 prediabetes syndrome Diseases 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
230000002265 prevention Effects 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
239000003472 antidiabetic agent Substances 0.000 claims description 5
229940126904 hypoglycaemic agent Drugs 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims 13
239000001257 hydrogen Substances 0.000 claims 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
229910052736 halogen Inorganic materials 0.000 claims 7
150000002367 halogens Chemical class 0.000 claims 7
150000002431 hydrogen Chemical class 0.000 claims 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 3
150000001875 compounds Chemical class 0.000 abstract description 165
230000000694 effects Effects 0.000 abstract description 26
125000005843 halogen group Chemical group 0.000 abstract description 14
239000000126 substance Substances 0.000 abstract description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 11
239000003814 drug Substances 0.000 abstract description 8
125000003396 thiol group Chemical group [H]S* 0.000 abstract description 7
230000007721 medicinal effect Effects 0.000 abstract 1
238000011321 prophylaxis Methods 0.000 abstract 1
238000000034 method Methods 0.000 description 86
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
235000008331 Pinus X rigitaeda Nutrition 0.000 description 47
235000011613 Pinus brutia Nutrition 0.000 description 47
241000018646 Pinus brutia Species 0.000 description 47
239000000243 solution Substances 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
239000000203 mixture Substances 0.000 description 39
239000007858 starting material Substances 0.000 description 38
230000015572 biosynthetic process Effects 0.000 description 31
238000003786 synthesis reaction Methods 0.000 description 31
125000003118 aryl group Chemical group 0.000 description 29
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
150000001299 aldehydes Chemical class 0.000 description 24
230000032258 transport Effects 0.000 description 24
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 23
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
150000001923 cyclic compounds Chemical class 0.000 description 17
235000002639 sodium chloride Nutrition 0.000 description 17
IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 16
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
238000010898 silica gel chromatography Methods 0.000 description 15
102000004877 Insulin Human genes 0.000 description 14
108090001061 Insulin Proteins 0.000 description 14
229940125396 insulin Drugs 0.000 description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
239000007787 solid Substances 0.000 description 14
239000002904 solvent Substances 0.000 description 13
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
230000009471 action Effects 0.000 description 11
238000001914 filtration Methods 0.000 description 11
239000000047 product Substances 0.000 description 11
125000003282 alkyl amino group Chemical group 0.000 description 10
125000006165 cyclic alkyl group Chemical group 0.000 description 10
238000000746 purification Methods 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
210000004369 blood Anatomy 0.000 description 9
239000008280 blood Substances 0.000 description 9
210000004027 cell Anatomy 0.000 description 9
238000000605 extraction Methods 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
RUXHWBMJNBBYNL-UHFFFAOYSA-N 3-hydroxy-1,2-dihydropyrrol-5-one Chemical compound OC1=CC(=O)NC1 RUXHWBMJNBBYNL-UHFFFAOYSA-N 0.000 description 8
ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
210000000577 adipose tissue Anatomy 0.000 description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
125000004414 alkyl thio group Chemical group 0.000 description 8
125000001072 heteroaryl group Chemical group 0.000 description 8
125000000623 heterocyclic group Chemical group 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
125000004093 cyano group Chemical group *C#N 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
239000002253 acid Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 5
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
235000011054 acetic acid Nutrition 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
239000013078 crystal Substances 0.000 description 5
229940079593 drug Drugs 0.000 description 5
230000002708 enhancing effect Effects 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000008103 glucose Substances 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
DOQJUNNMZNNQAD-UHFFFAOYSA-N pyrrolidine-2,4-dione Chemical compound O=C1CNC(=O)C1 DOQJUNNMZNNQAD-UHFFFAOYSA-N 0.000 description 5
239000000725 suspension Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 4
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
ZCGUVTAVRMRQOP-RKDXNWHRSA-N 3-[[(1r,2r)-2-aminocyclohexyl]amino]-1,2-dihydropyrrol-5-one Chemical compound N[C@@H]1CCCC[C@H]1NC1=CC(=O)NC1 ZCGUVTAVRMRQOP-RKDXNWHRSA-N 0.000 description 4
NRKQMDLBMZFWDM-UHFFFAOYSA-N 4-tert-butyl-2-chlorobenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C(Cl)=C1 NRKQMDLBMZFWDM-UHFFFAOYSA-N 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
125000000304 alkynyl group Chemical group 0.000 description 4
125000004104 aryloxy group Chemical group 0.000 description 4
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
238000003818 flash chromatography Methods 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
238000005406 washing Methods 0.000 description 4
FIZIXTUCOMHSRX-UHFFFAOYSA-N 2,4-dibutoxybenzaldehyde Chemical compound CCCCOC1=CC=C(C=O)C(OCCCC)=C1 FIZIXTUCOMHSRX-UHFFFAOYSA-N 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
SYCFYQFCFHKYPI-UHFFFAOYSA-N 4-(2-phenylethynyl)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C#CC1=CC=CC=C1 SYCFYQFCFHKYPI-UHFFFAOYSA-N 0.000 description 3
MGHIIGWDUVNPPV-UHFFFAOYSA-N 4-(4-nitrophenyl)benzaldehyde Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC=C(C=O)C=C1 MGHIIGWDUVNPPV-UHFFFAOYSA-N 0.000 description 3
XVBUHGDSGIKMMT-UHFFFAOYSA-N 4-butoxy-2-methoxybenzaldehyde Chemical compound CCCCOC1=CC=C(C=O)C(OC)=C1 XVBUHGDSGIKMMT-UHFFFAOYSA-N 0.000 description 3
SXGZIJOZHSTSAJ-UHFFFAOYSA-N 4-hexoxy-2-hydroxybenzaldehyde Chemical compound CCCCCCOC1=CC=C(C=O)C(O)=C1 SXGZIJOZHSTSAJ-UHFFFAOYSA-N 0.000 description 3
PPGRDLZPSDHBIC-UHFFFAOYSA-N 4-pyrazol-1-ylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1N1N=CC=C1 PPGRDLZPSDHBIC-UHFFFAOYSA-N 0.000 description 3
108091003079 Bovine Serum Albumin Proteins 0.000 description 3
229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
125000001769 aryl amino group Chemical group 0.000 description 3
125000003609 aryl vinyl group Chemical group 0.000 description 3
229940098773 bovine serum albumin Drugs 0.000 description 3
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
239000001768 carboxy methyl cellulose Substances 0.000 description 3
235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
239000008112 carboxymethyl-cellulose Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000005553 heteroaryloxy group Chemical group 0.000 description 3
230000002218 hypoglycaemic effect Effects 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
239000012528 membrane Substances 0.000 description 3
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 3
230000002093 peripheral effect Effects 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
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JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
235000011008 sodium phosphates Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
DSOWAKKSGYUMTF-GZOLSCHFSA-M sodium;(1e)-1-(6-methyl-2,4-dioxopyran-3-ylidene)ethanolate Chemical compound [Na+].C\C([O-])=C1/C(=O)OC(C)=CC1=O DSOWAKKSGYUMTF-GZOLSCHFSA-M 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000003462 vein Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Epidemiology (AREA)
Hematology (AREA)
Obesity (AREA)
Ophthalmology & Optometry (AREA)
Child & Adolescent Psychology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Cardiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Hydrogenated Pyridines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pyrrole Compounds (AREA)

RU2003116126/04A 2000-12-01 2001-11-29 Лактамные соединения и их фармацевтическое использование RU2287530C2 (ru)

Applications Claiming Priority (2)

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JP2000367175		2000-12-01
JP2000-367175		2000-12-01

Publications (2)

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RU2003116126A RU2003116126A (ru)	2004-11-27
RU2287530C2 true RU2287530C2 (ru)	2006-11-20

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US (3)	US7153850B2 (cs)
EP (1)	EP1346993B1 (cs)
JP (2)	JP3826400B2 (cs)
KR (1)	KR100826818B1 (cs)
CN (2)	CN1269818C (cs)
AT (1)	ATE446297T1 (cs)
AU (3)	AU1850202A (cs)
BG (1)	BG107857A (cs)
BR (1)	BR0115852A (cs)
CA (1)	CA2430124C (cs)
CZ (1)	CZ20031520A3 (cs)
DE (1)	DE60140270D1 (cs)
ES (1)	ES2331299T3 (cs)
HU (1)	HUP0400806A3 (cs)
IL (1)	IL156158A0 (cs)
MX (1)	MXPA03004876A (cs)
NO (1)	NO325401B1 (cs)
NZ (1)	NZ526164A (cs)
PL (1)	PL362835A1 (cs)
RU (1)	RU2287530C2 (cs)
SK (1)	SK6582003A3 (cs)
TW (1)	TWI241302B (cs)
UA (1)	UA76969C2 (cs)
WO (1)	WO2002044180A1 (cs)
YU (1)	YU42603A (cs)
ZA (1)	ZA200304100B (cs)

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MXPA05008363A (es)	2003-02-07	2005-12-06	Ajinomoto Kk	Agentes terapeuticos para diabetes.
WO2005042536A1 (ja) *	2003-10-31	2005-05-12	Ajinomoto Co., Inc.	複素環を有する新規縮合多環式化合物及びその医薬用途
CA2553329A1 (en)	2004-01-14	2005-07-28	Ajinomoto Co., Inc.	New fused polycyclic compounds
JP5056412B2 (ja)	2005-04-28	2012-10-24	味の素株式会社	新規ラクタム化合物
EP2157092A4 (en) *	2007-04-11	2011-04-13	Ajinomoto Kk	Remedy for diabetes
WO2008136394A1 (ja) *	2007-04-27	2008-11-13	Ajinomoto Co., Inc.	ラクタム化合物の製造方法及びその製造中間体
WO2008139574A1 (ja) *	2007-04-27	2008-11-20	Ajinomoto Co., Inc.	ラクタム化合物の結晶形およびその製造方法
WO2008139575A1 (ja) *	2007-04-27	2008-11-20	Ajinomoto Co., Inc.	経口投与用製剤
CN101619041B (zh) *	2008-07-02	2012-07-04	重庆华邦制药股份有限公司	一种二酮基含氮环化合物的合成方法及其中间体
JP2012180283A (ja) *	2009-07-02	2012-09-20	Ajinomoto Co Inc	ラクタム化合物の製造方法およびその製造中間体
JP2012180282A (ja) *	2009-07-02	2012-09-20	Ajinomoto Co Inc	ラクタム化合物の製造方法およびその製造中間体
EP3238723B1 (en) *	2014-12-22	2020-02-05	EA Pharma Co., Ltd.	Drug for treating disorders of corneal epithelium
WO2017127306A1 (en)	2016-01-18	2017-07-27	Arisan Therapeutics	Adamatane derivatives for the treatment of filovirus infection
US11548893B2 (en)	2017-07-15	2023-01-10	Arisan Therapeutics Inc.	Enantiomerically pure adamantane carboxamides for the treatment of filovirus infection
TWI820289B (zh) *	2019-01-23	2023-11-01	醣解生醫股份有限公司	β-內醯胺類化合物或其鹽於長效預防或治療葡萄糖代謝失調之用途

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2007
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Also Published As

Publication number	Publication date
HUP0400806A2 (hu)	2004-07-28
NO325401B1 (no)	2008-04-21
CA2430124C (en)	2011-01-11
PL362835A1 (en)	2004-11-02
ATE446297T1 (de)	2009-11-15
SK6582003A3 (en)	2003-09-11
CZ20031520A3 (cs)	2003-10-15
US7326701B2 (en)	2008-02-05
IL156158A0 (en)	2003-12-23
AU2002218502B2 (en)	2006-09-21
US7153850B2 (en)	2006-12-26
JPWO2002044180A1 (ja)	2004-04-02
CN1911915A (zh)	2007-02-14
US20040048847A1 (en)	2004-03-11
YU42603A (sh)	2006-03-03
KR100826818B1 (ko)	2008-05-02
NO20032439L (no)	2003-07-18
AU2006241377A1 (en)	2006-12-14
UA76969C2 (en)	2006-10-16
NO20032439D0 (no)	2003-05-28
US7632830B2 (en)	2009-12-15
AU1850202A (en)	2002-06-11
US20080096862A1 (en)	2008-04-24
CA2430124A1 (en)	2002-06-06
JP4505753B2 (ja)	2010-07-21
WO2002044180A1 (en)	2002-06-06
MXPA03004876A (es)	2004-01-27
BG107857A (bg)	2004-06-30
EP1346993A4 (en)	2005-12-21
CN100577651C (zh)	2010-01-06
EP1346993B1 (en)	2009-10-21
HUP0400806A3 (en)	2007-11-28
ZA200304100B (en)	2004-08-22
KR20030051893A (ko)	2003-06-25
ES2331299T3 (es)	2009-12-29
CN1487940A (zh)	2004-04-07
NZ526164A (en)	2004-09-24
CN1269818C (zh)	2006-08-16
JP3826400B2 (ja)	2006-09-27
US20060189597A1 (en)	2006-08-24
TWI241302B (en)	2005-10-11
EP1346993A1 (en)	2003-09-24
DE60140270D1 (de)	2009-12-03
BR0115852A (pt)	2003-12-23
JP2006213732A (ja)	2006-08-17
AU2006241377B2 (en)	2009-01-08

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RU2287530C2 - Лактамные соединения и их фармацевтическое использование - Google Patents

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